Chloroacetanilide

HCID 11485
NotesReactions
Substructure searchFind similar structures

Basic information

CAS
587-65-5
Standard SMILES
O=C(CCl)Nc1ccccc1
InChIKey
VONWPEXRCLHKRJ-UHFFFAOYSA-N
Molecular formula
C8H8ClNO
Average molar mass
169.61 g/mol
Monoisotopic mass
169.02944156

Names & identifiers

Preferred name
Chloroacetanilide
IUPAC
2-chloro-N-phenylacetamide
English name
2-Chloro-N-phenylacetamide
Molecular formula
C8H8ClNO
Molecular weight
169.61

Names & synonyms

2-CHLORO-N-PHENYLACETAMIDE2-Chloroacetanilide587-65-5ChloroacetanilideN-PhenylchloroacetamideN-Phenyl-2-chloroacetamideAcetanilide, 2-chloro-DTXSID3041409alpha-Chloroacetanilide2R6RM9R0W8NSC-311DTXCID1021409
Show more names
SKL808AKOS B015615ART-CHEM-BB B0156152-chloro-acetanilidDiclofenac Impurity 24Paracetamol Impurity 8N-(CHLOROACETYL)ANILINE
RefChem:86436209-604-0Acetamide, 2-chloro-N-phenyl-MFCD00018887.alpha.-ChloroacetanilideNSC 311Diclofenac Impurity T.omega.-Chloroacetanilide

Database identifiers

CAS
587-65-5
PubChem CID
11485
DTXSID
DTXSID3041409
ChEMBL
CHEMBL2164307
UNII
2R6RM9R0W8
EC Number
209-604-0
Nikkaji
J33.441C

Properties

Computed structural properties

XLogP
1.6
Topological polar surface area
29.1 Ų
Hydrogen bond donors
1
Hydrogen bond acceptors
1
Rotatable bonds
2
Heavy atoms
11

Experimental & physicochemical properties

Chemical ClassesNitrogen Compounds -> Other Aromatics (Nitrogen)
SpringerMaterials PropertiesNuclear quadrupole resonance spectroscopy
LogP · 2 items

Log P= 1.63

1.63

Color/FormVery light beige, crystalline powder
SolubilityPractically insoluble
Melting Point86-88 °C

Physicochemical properties

Melting point
136 · 136-139 °C (lit.)
Boiling point
340 · 340.0±25.0 °C(Predicted)
Density
1.266 · 1.266±0.06 g/cm3(Predicted)
storage temp.
Keep in dark place,Sealed in dry,Room Temperature
solubility
Chloroform (Slightly), Methanol (Slightly)
form
Solid

Safety & regulation

GHS classification

GHS Classification · 4 items

Warning

H315 (95.1%): Causes skin irritation [Warning Skin corrosion/irritation]

P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 41 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Hazards SummaryAn irritant; May induce methemoglobinemia; [Aldrich MSDS]
Hazard Classes and CategoriesSkin Irrit. 2 (95.1%)

Safety & protection

Disposal Methods · 1 item

SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

Toxicology

Adverse EffectsMethemoglobinemia - The presence of increased methemoglobin in the blood; the compound is classified as secondary toxic effect
Non-Human Toxicity Excerpts · 2 items

2-CHLORO-N-PHENYLACETAMIDE SHOWED RELATIVELY WEAK CHOLINE ACETYLTRANSFERASE INHIBITION ACTIVITY.

The effects of 2-chloroacetanilide (2-CAA), 3-chloroacetanilide (3-CAA) and 4-chloroacetanilide (4-CAA) on liver and kidney function and morphology were examined in rats. Male Fischer 344 rats were given a single ip injection of a chloroacetanilide at 0.5, 1.0 or 1.5 millimole/kg. Renal function was monitored for 24 or 48 hr following dosing. At 24 or 48 hr, liver function and tissue morphology were determined. At the two lower dose levels,all three chloroacetanilide isomers decr food and water intake on day 1 after treatment. Food intake remained depressed in 2-CAA and 3-CAA treated animals on the second day, but water intake was normal. Urinary protein excretion on day 1 was incr only in rats treated with 4-CAA. Blood urea nitrogen concn was not incr in any group at 48 hr while kidney weight was incr only in the 3-CAA treated group. Hepatic weight was incr at 48 hr in rats treated with 3-CAA and 4-CAA. Plasma alanine aminotransferase activity was incr at 48 hr only in the 4-CAA group. In additional studies, renal cortical slices from untreated rats were incubated with a chloroacetanilide or vehicle and the effect on organic ion accumulation was determined. Chloroacetanilides were shown to directly alter renal function in an isomer specific manner.

Safety data

PPE
dust mask type N95 (US), Eyeshields, Gloves
wgk
3
rtecs
AE1000000
hs_code
2921420090
risk_code
36/37/38
Signal word
Warning

Chemistry & industry

Uses & manufacturing

UsesNot commercially produced in the US; [HSDB]
U.S. Exports · 2 items

(1977) No Data

(1979) No Data

U.S. Imports · 2 items

(1977) No Data

(1979) No Data

U.S. Production · 2 items

(1977) NOT PRODUCED COMMERCIALLY IN US

(1979) NOT PRODUCED COMMERCIALLY IN US

Applications · 3 items

Uses2-Chloro-N-phenylacetamide is used as a reagent in the synthesis of indolylmethylene benzo[h]thiazolo[2,3-b]quinazolinones which exhibit anticancer and antimicrobial activities in vitro.

Uses2-Chloro-N-phenylacetamide may be used in the preparation of N,N′-(ethane-1,2-diyl)bis(2-(2-oxo-2-(phenylamino)ethoxy)benzamide), an amide podand. It may also be used to prepare phenylacetamide-based Schiff base ligands by reacting with corresponding hydrazones.

General Description2-Chloro-N-phenylacetamide, also known as chloroacetanilide, can be prepared by reacting aniline with chloroacetylchloride in glacial acetic acid. The analysis of its crystal structure shows the presence of N-H...O hydrogen bonds between the molecules.

Upstream & downstream products

Suppliers99 total

郑州阿尔法化工有限公司+86-18530059196 · [email protected]
北京福源坊科技有限公司010-57903446 15869909019 · [email protected]
Hebei Chuanghai Biotechnology Co., Ltd+86-17732866630 · [email protected]
艾吉析科技（上海）有限公司17717235263 · [email protected]
上海麦克林生化科技股份有限公司021-50706066 15221275939 · [email protected]

Related reactions

91 records
New reaction record

Compound notes

Loading…