2-Chloroacetophenone

  2-Chloroacetophenone (CAS No.532-27-4) was reported in EPA TSCA Inventory. Community Right-To-Know List.

OSHA PEL: TWA 0.05 ppm
ACGIH TLV: TWA 0.05 ppm; Not Classifiable as a Human Carcinogen
DOT Classification:  6.1; Label: Poison

The 2-Chloroacetophenone with CAS registry number of 532-27-4 is also known as 1-Phenyl-2-chloro-1-ethanone. The IUPAC name is 2-Chloro-1-phenylethanone. It belongs to product categories of Acetylhalide. Its EINECS registry number is 208-531-1. In addition, the formula is C₈H₇ClO and the molecular weight is 154.59. This chemical is a white or light yellow crystal and should be stored in cool, dry and ventilated away from fire and heat.

Physical properties about 2-Chloroacetophenone are: (1)ACD/LogP: 1.85; (2)ACD/LogD (pH 5.5): 1.85; (3)ACD/LogD (pH 7.4): 1.85; (4)ACD/BCF (pH 5.5): 14.93; (5)ACD/BCF (pH 7.4): 14.93; (6)ACD/KOC (pH 5.5): 240.95; (7)ACD/KOC (pH 7.4): 240.95; (8)#H bond acceptors: 1; (9)#H bond donors: 0; (10)#Freely Rotating Bonds: 2; (11)Index of Refraction: 1.533; (12)Molar Refractivity: 41.12 cm³; (13)Molar Volume: 132.3 cm³; (14)Surface Tension: 39 dyne/cm; (15)Density: 1.168 g/cm³; (16)Flash Point: 104.8 °C; (17)Enthalpy of Vaporization: 48.16 kJ/mol; (18)Boiling Point: 244.5 °C at 760 mmHg; (19)Vapour Pressure: 0.0303 mmHg at 25 °C.

Preparation of 2-Chloroacetophenone: it can be synthesized by the friedel-crafts acylation of benzene and chloroacetyl chloride with an aluminium chloride catalyst.

Uses of 2-Chloroacetophenone: it is used as pharmaceutical intermediate and for organic synthesis. What's more, it is used to produce 2-chloromethyl-2-phenyl-[1,3]dioxolane by reaction with ethane-1,2-diol. The reaction needs reagent chlorotrimethylsilane at ambient temperature for 16 hours and the yield is about 99%.

When you are using this chemical, please be cautious about it. As a chemical, it is irritating to eyes, respiratory system and skin. It is toxic by inhalation, in contact with skin and if swallowed that may cause sensitisation. During using it, wear suitable protective clothing, gloves and eye/face protection. Keep container tightly closed and in a well-ventilated place and do not breathe dust. If contact with eyes accidently, rinse immediately with plenty of water and seek medical advice. In case of accident or if you feel unwell seek medical advice immediately.

You can still convert the following datas into molecular structure:
1. Canonical SMILES: C1=CC=C(C=C1)C(=O)CCl
2. InChI: InChI=1S/C8H7ClO/c9-6-8(10)7-4-2-1-3-5-7/h1-5H,6H2
3. InChIKey: IMACFCSSMIZSPP-UHFFFAOYSA-N

The toxicity data is as follows:

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
guinea pig	LCLo	inhalation	490mg/m3/30M (490mg/m3)	SENSE ORGANS AND SPECIAL SENSES: OTHER CHANGES: OLFACTION LUNGS, THORAX, OR RESPIRATION: ACUTE PULMONARY EDEMA BLOOD: HEMORRHAGE	Archives of Toxicology. Vol. 40, Pg. 75, 1978.
guinea pig	LD50	intraperitoneal	17mg/kg (17mg/kg)	BEHAVIORAL: COMA LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES SKIN AND APPENDAGES (SKIN): HAIR: OTHER	Archives of Toxicology. Vol. 40, Pg. 75, 1978.
guinea pig	LD50	oral	158mg/kg (158mg/kg)	BEHAVIORAL: COMA LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES SKIN AND APPENDAGES (SKIN): HAIR: OTHER	Archives of Toxicology. Vol. 40, Pg. 75, 1978.
guinea pig	LD50	skin	> 1gm/kg (1000mg/kg)		National Technical Information Service. Vol. OTS0556684,
human	LCLo	inhalation	159mg/m3/20M (159mg/m3)		"Toxicology of Drugs and Chemicals," Deichmann, W.B., New York, Academic Press, Inc., 1969Vol. -, Pg. 163, 1969.
human	TCLo	inhalation	20mg/m3 (20mg/m3)	SENSE ORGANS AND SPECIAL SENSES: OTHER: EYE LUNGS, THORAX, OR RESPIRATION: DYSPNEA LUNGS, THORAX, OR RESPIRATION: COUGH	British Journal of Industrial Medicine. Vol. 29, Pg. 298, 1972.
human	TCLo	inhalation	93mg/m3/3M (93mg/m3)	SENSE ORGANS AND SPECIAL SENSES: LACRIMATION: EYE SENSE ORGANS AND SPECIAL SENSES: CONJUNCTIVE IRRITATION: EYE LUNGS, THORAX, OR RESPIRATION: DYSPNEA	American Industrial Hygiene Association Journal. Vol. 23, Pg. 199, 1962.
mouse	LC50	inhalation	59mg/m3 (59mg/m3)		Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 58(10), Pg. 4, 1993.
mouse	LD50	intraperitoneal	60mg/kg (60mg/kg)		National Technical Information Service. Vol. AD837-111,
mouse	LD50	intravenous	81mg/kg (81mg/kg)	BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD LUNGS, THORAX, OR RESPIRATION: RESPIRATORY STIMULATION KIDNEY, URETER, AND BLADDER: OTHER CHANGES	Archives of Toxicology. Vol. 40, Pg. 75, 1978.
mouse	LD50	oral	139mg/kg (139mg/kg)		National Technical Information Service. Vol. AD837-111,
rabbit	LCLo	inhalation	465mg/m3/20M (465mg/m3)	SENSE ORGANS AND SPECIAL SENSES: OTHER CHANGES: OLFACTION BLOOD: HEMORRHAGE LUNGS, THORAX, OR RESPIRATION: ACUTE PULMONARY EDEMA	Archives of Toxicology. Vol. 40, Pg. 75, 1978.
rabbit	LD50	intravenous	30mg/kg (30mg/kg)	BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD LUNGS, THORAX, OR RESPIRATION: RESPIRATORY STIMULATION KIDNEY, URETER, AND BLADDER: OTHER CHANGES	Archives of Toxicology. Vol. 40, Pg. 75, 1978.
rabbit	LD50	oral	118mg/kg (118mg/kg)	BEHAVIORAL: COMA LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES SKIN AND APPENDAGES (SKIN): HAIR: OTHER	Archives of Toxicology. Vol. 40, Pg. 75, 1978.
rat	LCLo	inhalation	417mg/m3/15M (417mg/m3)	SENSE ORGANS AND SPECIAL SENSES: OTHER CHANGES: OLFACTION LUNGS, THORAX, OR RESPIRATION: ACUTE PULMONARY EDEMA BLOOD: HEMORRHAGE	Archives of Toxicology. Vol. 40, Pg. 75, 1978.
rat	LD50	intraperitoneal	36mg/kg (36mg/kg)	BEHAVIORAL: COMA SKIN AND APPENDAGES (SKIN): HAIR: OTHER LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES	Archives of Toxicology. Vol. 40, Pg. 75, 1978.
rat	LD50	intravenous	41mg/kg (41mg/kg)	BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD LUNGS, THORAX, OR RESPIRATION: RESPIRATORY STIMULATION KIDNEY, URETER, AND BLADDER: OTHER CHANGES	Archives of Toxicology. Vol. 40, Pg. 75, 1978.
rat	LD50	oral	50mg/kg (50mg/kg)		Toxicology and Applied Pharmacology. Vol. 17, Pg. 295, 1970.