1,1-Dichloropinacolin

Reported in EPA TSCA Inventory.

DOT Classification:  3; Label: Flammable Liquid

The 2-Butanone,1,1-dichloro-3,3-dimethyl-, with the CAS registry number 22591-21-5, is also known as Dichloropinacolin. Its EINECS number is 245-111-7. This chemical's molecular formula is C₆H₁₀Cl₂O and molecular weight is 169.05. What's more, its systematic name is 1,1-dichloro-3,3-dimethylbutan-2-one. It is mainly used as medicine and pesticide intermediates, especially an intermediate of phytocide Metribuzin.

Physical properties of 2-Butanone,1,1-dichloro-3,3-dimethyl- are: (1)ACD/LogP: 2.59; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 2.59; (4)ACD/LogD (pH 7.4): 2.59; (5)ACD/BCF (pH 5.5): 54.44; (6)ACD/BCF (pH 7.4): 54.44; (7)ACD/KOC (pH 5.5): 608.38; (8)ACD/KOC (pH 7.4): 608.38; (9)#H bond acceptors: 1; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 2; (12)Polar Surface Area: 17.07 Å²; (13)Index of Refraction: 1.446; (14)Molar Refractivity: 39.49 cm³; (15)Molar Volume: 147.8 cm³; (16)Polarizability: 15.65×10^-24cm³; (17)Surface Tension: 29.7 dyne/cm; (18)Density: 1.143 g/cm³; (19)Flash Point: 65 °C; (20)Enthalpy of Vaporization: 41.01 kJ/mol; (21)Boiling Point: 173.8 °C at 760 mmHg; (22)Vapour Pressure: 1.25 mmHg at 25°C.

Preparation: this chemical can be prepared by 3,3-dimethyl-butan-2-one at the temperature of 70 °C. This reaction will need reagents benzyltrimethylammonium tetrachloroiodate, acetic acid with the reaction time of 3 hours. The yield is about 47%.

Uses of 2-Butanone,1,1-dichloro-3,3-dimethyl-: it can be used to produce 1-tert-butyl-2,2-dichlorovinyl ethyl phosphorochloridite at the temperature of 20 °C. It will need reagent Et₃N. The yield is about 72%.

You can still convert the following datas into molecular structure:
(1)SMILES: ClC(Cl)C(=O)C(C)(C)C
(2)Std. InChI: InChI=1S/C6H10Cl2O/c1-6(2,3)4(9)5(7)8/h5H,1-3H3
(3)Std. InChIKey: UDWZXMQIEHAAQT-UHFFFAOYSA-N

The toxicity data is as follows: 

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
guinea pig	LDLo	subcutaneous	2gm/kg (2000mg/kg)	PERIPHERAL NERVE AND SENSATION: FLACCID PARALYSIS WITHOUT ANESTHESIA (USUALLY NEUROMUSCULAR BLOCKAGE) LUNGS, THORAX, OR RESPIRATION: DYSPNEA	"Studien uber die Pharmakologie des Pinakolins und einiger seiner Derivate mit besonderer Berucksichtigung der Kreislaufwirkung, Dissertation," Bang, L., Pharmakologischen Abteilung des Karolinischen Instituts, Stockholm, Sweden, 1934Vol. -, Pg. -, 1934.
hamster	LC50	inhalation	> 1234mg/m3/4H (1234mg/m3)	SENSE ORGANS AND SPECIAL SENSES: OTHER: EYE LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES	National Technical Information Service. Vol. OTS0571099,
mouse	LC50	inhalation	643mg/m3/4H (643mg/m3)	SENSE ORGANS AND SPECIAL SENSES: OTHER: EYE LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES	National Technical Information Service. Vol. OTS0571099,
mouse	LD50	oral	4150mg/kg (4150mg/kg)	BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX) BEHAVIORAL: MUSCLE WEAKNESS BEHAVIORAL: WITHDRAWAL	Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 52(12), Pg. 92, 1987.
rabbit	LC50	inhalation	1234mg/m3/4H (1234mg/m3)	SENSE ORGANS AND SPECIAL SENSES: OTHER: EYE LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES	National Technical Information Service. Vol. OTS0571099,
rabbit	LD50	oral	3550mg/kg (3550mg/kg)	BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX) BEHAVIORAL: WITHDRAWAL BEHAVIORAL: MUSCLE WEAKNESS	Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 52(12), Pg. 92, 1987.
rat	LC50	inhalation	643mg/m3/4H (643mg/m3)	SENSE ORGANS AND SPECIAL SENSES: OTHER: EYE LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES	National Technical Information Service. Vol. OTS0571099,
rat	LD50	oral	1300mg/kg (1300mg/kg)	LUNGS, THORAX, OR RESPIRATION: DYSPNEA GASTROINTESTINAL: OTHER CHANGES BLOOD: HEMORRHAGE	National Technical Information Service. Vol. OTS0571099,
rat	LD50	skin	5gm/kg (5000mg/kg)	LUNGS, THORAX, OR RESPIRATION: DYSPNEA GASTROINTESTINAL: OTHER CHANGES BLOOD: HEMORRHAGE	National Technical Information Service. Vol. OTS0571099,