NP-MRD: Showing NP-Card for alpha-Chloroacetophenone (NP0045085)

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Record Information

Version

2.0

Created at

2022-03-10 18:57:42 UTC

Updated at

2022-03-10 22:17:59 UTC

NP-MRD ID

NP0045085

Secondary Accession Numbers

None

Natural Product Identification

Common Name

alpha-Chloroacetophenone

Description

Alpha-Chloroacetophenone or 2-Chloroacetophenone, also known as mace, belongs to the class of organic compounds known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group. Alpha-Chloroacetophenone is a useful building block in organic chemistry. Although it is potentially a toxic compound, alpha-chloroacetophenone is commonly used as a tear gas. Due to its peripheral sensory irritant effect, it has been historically used as a riot control agent. Alpha-Chloroacetophenone is synthesized by the Friedel-Crafts acylation of benzene using chloroacetyl chloride, with an aluminium chloride catalyst.

Structure

MOL 3D MOL SDF PDB SMILES InChI

10757
  Mrv1652303202019002D          

 17 17  0  0  0  0            999 V2000
    3.0790    1.8563    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    1.0313    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -0.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790   -0.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    0.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -1.4438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790   -1.4438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -1.8563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790    1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2071   -0.3630    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5220   -0.3630    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2071   -1.6995    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5220   -1.6995    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -2.3678    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2540    0.5506    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5827    1.1201    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1 10  1  0  0  0  0
  2  6  2  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  3  6  1  0  0  0  0
  4  7  1  0  0  0  0
  4 11  1  0  0  0  0
  5  8  2  0  0  0  0
  5 12  1  0  0  0  0
  6 10  1  0  0  0  0
  7  9  2  0  0  0  0
  7 13  1  0  0  0  0
  8  9  1  0  0  0  0
  8 14  1  0  0  0  0
  9 15  1  0  0  0  0
 10 16  1  0  0  0  0
 10 17  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0045085

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]C1=C([H])C([H])=C(C([H])=C1[H])C(=O)C([H])([H])Cl

> <INCHI_IDENTIFIER>
InChI=1S/C8H7ClO/c9-6-8(10)7-4-2-1-3-5-7/h1-5H,6H2

> <INCHI_KEY>
IMACFCSSMIZSPP-UHFFFAOYSA-N

> <FORMULA>
C8H7ClO

> <MOLECULAR_WEIGHT>
154.594

> <EXACT_MASS>
154.018542553

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
17

> <JCHEM_AVERAGE_POLARIZABILITY>
15.060341244543498

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-chloro-1-phenylethan-1-one

> <ALOGPS_LOGP>
1.90

> <JCHEM_LOGP>
2.068237144666667

> <ALOGPS_LOGS>
-2.63

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.370267906027696

> <JCHEM_PKA_STRONGEST_BASIC>
-7.71496265346217

> <JCHEM_POLAR_SURFACE_AREA>
17.07

> <JCHEM_REFRACTIVITY>
41.214

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.59e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
phenacyl chloride

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 20-MAR-20   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 10757                                             
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-MAR-20         0                                  
HETATM    1 Cl   UNK     0       5.747   3.465   0.000  0.00  0.00          Cl+0
HETATM    2  O   UNK     0       3.080   1.925   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       4.414  -0.385   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.080  -1.155   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.747  -1.155   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.414   1.155   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.080  -2.695   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.747  -2.695   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.414  -3.465   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.747   1.925   0.000  0.00  0.00           C+0
HETATM   11  H   UNK     0       2.253  -0.678   0.000  0.00  0.00           H+0
HETATM   12  H   UNK     0       6.574  -0.678   0.000  0.00  0.00           H+0
HETATM   13  H   UNK     0       2.253  -3.172   0.000  0.00  0.00           H+0
HETATM   14  H   UNK     0       6.574  -3.172   0.000  0.00  0.00           H+0
HETATM   15  H   UNK     0       4.414  -4.420   0.000  0.00  0.00           H+0
HETATM   16  H   UNK     0       6.074   1.028   0.000  0.00  0.00           H+0
HETATM   17  H   UNK     0       6.688   2.091   0.000  0.00  0.00           H+0
CONECT    1   10                                                            
CONECT    2    6                                                            
CONECT    3    4    5    6                                                  
CONECT    4    3    7   11                                                  
CONECT    5    3    8   12                                                  
CONECT    6    2    3   10                                                  
CONECT    7    4    9   13                                                  
CONECT    8    5    9   14                                                  
CONECT    9    7    8   15                                                  
CONECT   10    1    6   16   17                                             
CONECT   11    4                                                            
CONECT   12    5                                                            
CONECT   13    7                                                            
CONECT   14    8                                                            
CONECT   15    9                                                            
CONECT   16   10                                                            
CONECT   17   10                                                            
MASTER        0    0    0    0    0    0    0    0   17    0   34    0
END

View in JSmol

Synonyms

Value	Source
1-Chloroacetophenone	ChEMBL
2 Chloroacetophenone	MeSH
Mace	MeSH
2 chloro 1 Phenylethanone	MeSH
2-chloro-1-Phenylethanone	MeSH
Chloracetophenone	MeSH
Chloroacetophenone	MeSH
Omega chloroacetophenone	MeSH
Omega-chloroacetophenone	MeSH
3'-Chloroacetophenone	MeSH
alpha Chloroacetophenone	MeSH
alpha-Chloroacetophenone	MeSH
3' Chloroacetophenone	MeSH

Chemical Formula

C₈H₇ClO

Average Mass

154.5940 Da

Monoisotopic Mass

154.01854 Da

IUPAC Name

2-chloro-1-phenylethan-1-one

Traditional Name

phenacyl chloride

CAS Registry Number

532-27-4

SMILES

[H]C1=C([H])C([H])=C(C([H])=C1[H])C(=O)C([H])([H])Cl

InChI Identifier

InChI=1S/C8H7ClO/c9-6-8(10)7-4-2-1-3-5-7/h1-5H,6H2

InChI Key

IMACFCSSMIZSPP-UHFFFAOYSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25.16 MHz, CDCl₃, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Cannabis sativa	NULL	Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Alkyl-phenylketones

Alternative Parents

Substituents

Alkyl-phenylketone
Aryl alkyl ketone
Benzoyl
Benzenoid
Monocyclic benzene moiety
Alpha-haloketone
Alpha-chloroketone
Organic oxide
Hydrocarbon derivative
Organochloride
Organohalogen compound
Alkyl halide
Alkyl chloride
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	1.9	ALOGPS
logP	2.07	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	15.37	ChemAxon
pKa (Strongest Basic)	-7.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	17.07 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	41.21 m³·mol⁻¹	ChemAxon
Polarizability	15.06 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Phenacyl chloride

METLIN ID

Not Available

PubChem Compound

10757

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for alpha-Chloroacetophenone (NP0045085)

MOL for NP0045085 (alpha-Chloroacetophenone)

3D MOL for NP0045085 (alpha-Chloroacetophenone)

3D SDF for NP0045085 (alpha-Chloroacetophenone)

3D-SDF for NP0045085 (alpha-Chloroacetophenone)

PDB for NP0045085 (alpha-Chloroacetophenone)

3D PDB for NP0045085 (alpha-Chloroacetophenone)

SMILES for NP0045085 (alpha-Chloroacetophenone)

INCHI for NP0045085 (alpha-Chloroacetophenone)

Structure for NP0045085 (alpha-Chloroacetophenone)

3D Structure for NP0045085 (alpha-Chloroacetophenone)