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55-98-1

Basic Information
CAS No.: 55-98-1
Name: Busulfan
Article Data: 23
Molecular Structure:
Molecular Structure of 55-98-1 (Busulfan)
Formula: C6H14O6S2
Molecular Weight: 246.306
Synonyms: 1,4-Butanediol,dimethanesulfonate (8CI,9CI);Methanesulfonic acid, tetramethylene ester (6CI);1,4-Butanediol dimesylate;Busilvex;Busulphan;Citosulfan;GT 2041;GT 41;Glyzophrol;Leucosulfan;Mielevcin;Mielucin;Mileran;Misulban;Myeloleukon;Mylecytan;Sulfabutin;Tetramethylene bis[methanesulfonate];
EINECS: 200-250-2
Density: 1.35 g/cm3
Melting Point: 114-118 °C
Boiling Point: 464 °C at 760 mmHg
Flash Point: 234.4 °C
Solubility: Decomposes in water
Appearance: white crystalline solid
Hazard Symbols: VeryT+,ToxicT
Risk Codes: 45-26/27/28-63-46-36/37/38-23/24/25
Safety: 53-36/37/39-45-28A
Transport Information: UN 2811 6.1/PG 1
PSA: 103.50000
LogP: 1.88060
Synthetic route
110-63-4

Butane-1,4-diol

3144-09-0

methanesulfonamide

55-98-1

busulfan

Conditions
ConditionsYield
With triethylamine at 5 - 40℃; for 4h; Temperature;91%
110-63-4

Butane-1,4-diol

124-63-0

methanesulfonyl chloride

55-98-1

busulfan

Conditions
ConditionsYield
With triethylamine In dichloromethane at 10 - 20℃; for 24h;86%
With triethylamine In dichloromethane at 0 - 20℃; for 4h;73.52%
With pyridine at 25℃; for 2h;55%
109-99-9

tetrahydrofuran

41138-92-5

methanesulfonyl bromide

A

110-52-1

1,4-dibromo-butane

B

7239-41-0

4,4'-dibromo-di-n-butyl ether

C

55-98-1

busulfan

D

40671-33-8

1-bromo-4-methanesulfonyloxy-butane

Conditions
ConditionsYield
zinc(II) chloride at 75℃; for 5h;
40671-33-8

1-bromo-4-methanesulfonyloxy-butane

2386-52-9

silver methanesulfonate

55-98-1

busulfan

Conditions
ConditionsYield
In acetonitrile for 5h; Heating;
110-63-4

Butane-1,4-diol

7143-01-3

Methanesulfonic anhydride

55-98-1

busulfan

18001-91-7

bistrimethyl(1,4-butanedioxy)silane

124-63-0

methanesulfonyl chloride

55-98-1

busulfan

Conditions
ConditionsYield
With tin(IV) chloride at 80 - 100℃;
96042-30-7

4-(dicyanomethylene)-2-methyl-6-(p-dimethylaminostyryl)-4H-pyran

124-63-0

methanesulfonyl chloride

55-98-1

busulfan

Conditions
ConditionsYield
With triethylamine In water; ethyl acetate
55-98-1

busulfan

1182838-48-7

1,10-N,N'-bis-[cyclomaltoheptaosyl-6A-deoxy-6A-ureido]-4,7,13,16-tetraoxa-1,10-diazacyclooctadecane

1182838-51-2

C6H14O6S2*C98H164N4O74

Conditions
ConditionsYield
In water; dimethyl sulfoxide at 20℃; for 18h; Inert atmosphere;100%
55-98-1

busulfan

1182838-47-6

1,10-N,N'-bis-(β-D-ureidocellobiosyl)-4,7,13,16-tetraoxa-1,10-diazacyclooctadecane

1182838-49-8

C6H14O6S2*C38H68N4O26

Conditions
ConditionsYield
In water; dimethyl sulfoxide at 20℃; for 18h; Inert atmosphere;100%
55-98-1

busulfan

138566-17-3

2-(benzhydrylideneamino)-1-(10,10-dimethyl-3,3-dioxo-3λ6-thia-4-aza-tricyclo[5.2.1.01.5]dec-4-yl)ethanone

C16H26N2O3S

Conditions
ConditionsYield
Stage #1: 2-(benzhydrylideneamino)-1-(10,10-dimethyl-3,3-dioxo-3λ6-thia-4-aza-tricyclo[5.2.1.01.5]dec-4-yl)ethanone With lithium hexamethyldisilazane In tetrahydrofuran at -78℃; for 0.333333h; Inert atmosphere;
Stage #2: busulfan In tetrahydrofuran at -78℃; for 3.16667h;
83%
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    Product name: Busulfan CAS No.: 55-98-1 Molecule Formula:C6H14O6S2 Molecule Weight:246.30 Purity: 99.0% Package: 25kg/drum Description:White crystalline powder Manufacture Standards:Enterprise Standard TESTING ITEMS

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Chemistry

Structure of Busulfan (CAS NO.55-98-1):

IUPAC Name: 4-methylsulfonyloxybutyl methanesulfonate
Molecular Formula: C6H14O6S2
Molar mass: 246.30176 g/mol
H bond acceptors: 6
H bond donors: 0
Freely Rotating Bonds: 7
Polar Surface Area: 103.5Å2
Index of Refraction: 1.47
Molar Refractivity: 50.94 cm3
Molar Volume: 182.3 cm3
Surface Tension: 46.6 dyne/cm
Density: 1.35 g/cm3
Flash Point: 234.4 °C
Enthalpy of Vaporization: 69.75 kJ/mol
Boiling Point: 464 °C at 760 mmHg
Vapour Pressure: 2.41E-08 mmHg at 25°C
Appearance: White Crystalline Solid
Melting point: 114-118°C
Solubility: Solubility in acetone at 25 °C for 2.4g/100ml, in ethanol solubility for 0.1g/100ml, almost no smell.
Water solubility:Decomposes

History

  Busulfan was the mainstay of the chemotherapeutic treatment of Chronic Myeloid Leukemia (CML) until it was displaced by the new gold standard, Imatinib, though it is still in use to a degree as a result of the drug's relative inexpense.

 

Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
bird - wild LD50 oral 56200ug/kg (56.2mg/kg)   Archives of Environmental Contamination and Toxicology. Vol. 12, Pg. 355, 1983.
dog LDLo intravenous 8mg/kg (8mg/kg) BLOOD: LEUKOPENIA

BLOOD: AGRANULOCYTOSIS

BLOOD: OTHER CHANGES
Cancer Chemotherapy Reports, Part 2. Vol. 2, Pg. 203, 1965.
man TDLo oral 8mg/kg/2D-I (8mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD Lancet. Vol. 2, Pg. 1463, 1984.
monkey LDLo intravenous 8mg/kg (8mg/kg) BLOOD: LEUKOPENIA

BLOOD: OTHER CHANGES

BLOOD: AGRANULOCYTOSIS
Cancer Chemotherapy Reports, Part 2. Vol. 2, Pg. 203, 1965.
mouse LD50 intraperitoneal 86mg/kg (86mg/kg) SENSE ORGANS AND SPECIAL SENSES: OTHER CHANGES: OLFACTION

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"
Kiso to Rinsho. Clinical Report. Vol. 5, Pg. 1894, 1971.
mouse LD50 oral 110mg/kg (110mg/kg) GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"

SKIN AND APPENDAGES (SKIN): HAIR: OTHER
Kiso to Rinsho. Clinical Report. Vol. 5, Pg. 1894, 1971.
mouse LD50 subcutaneous 63mg/kg (63mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"
Kiso to Rinsho. Clinical Report. Vol. 5, Pg. 1894, 1971.
mouse LD50 unreported 46mg/kg (46mg/kg)   British Journal of Cancer. Vol. 6, Pg. 160, 1952.
rat LD50 intraperitoneal 18mg/kg (18mg/kg) GASTROINTESTINAL: OTHER CHANGES

BLOOD: CHANGES IN BONE MARROW NOT INCLUDED ABOVE
Biochemical Pharmacology. Vol. 1, Pg. 39, 1958.
rat LD50 intravenous 1800ug/kg (1.8mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 20, Pg. 1467, 1970.
rat LD50 subcutaneous 22mg/kg (22mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"
Kiso to Rinsho. Clinical Report. Vol. 5, Pg. 1894, 1971.
rat LD50 unreported 10mg/kg (10mg/kg)   Chemical Abstracts. Vol. 55, Pg. 10679a, 1961.
rat LDLo oral 15mg/kg (15mg/kg)   Khimiya i Meditsina. Vol. 13, Pg. 34, 1960.
women TDLo oral 80mg/kg/8Y (80mg/kg) SENSE ORGANS AND SPECIAL SENSES: OTHER: EYE

VASCULAR: REGIONAL OR GENERAL ARTERIOLAR OR VENOUS DILATION

GASTROINTESTINAL: CHANGES IN STRUCTURE OR FUNCTION OF SALIVARY GLANDS
JAMA, Journal of the American Medical Association. Vol. 238, Pg. 1951, 1977.
 

Consensus Reports

NTP 10th Report on Carcinogens. IARC Cancer Review: Group 1 IMEMDT    IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 7 (1987),p. 137.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.: ) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) ; Animal Inadequate Evidence IMEMDT    IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 4 (1974),p. 247.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.: ) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) ; Human Inadequate Evidence IMEMDT    IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 4 (1974),p. 247.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.: ) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) . EPA Genetic Toxicology Program.

Safety Profile

Confirmed carcinogen producing leukemia, kidney, and uterine tumors. Experimental neoplastigenic and tumorigenic data. Poison by ingestion, subcutaneous, intraperitoneal, intravenous, and possibly other routes. Ingestion by pregnant women can cause cancer of the reproductive system of the fetus including the uterus. Human teratogenic effects by ingestion and possibly other routes include developmental abnormalities of the eye, ear, craniofacial area including the nose and tongue, gastrointestinal system, endocrine system, urogenital system, and other unspecified areas. Other human reproductive effects by ingestion and possibly other routes include: impotence, changes in the uterus, cervix, and vagina, and menstrual-cycle disorders. Experimental reproductive effects. Human systemic effects by ingestion: general arteriolar or venous dilation of the eye, changes in structure or function of salivary glands. When heated to decomposition it emits toxic fumes of SOx. See also Hazard SULFONATES.
Codes: T+,T
Risk Statements:
23:  Toxic by inhalation
24:  Toxic in contact with skin
25:  Toxic if swallowed
26:  Very Toxic by inhalation
27:  Very Toxic in contact with skin
28:  Very Toxic if swallowed
36:  Irritating to the eyes
37:  Irritating to the respiratory system
38:  Irritating to the skin
45:  May cause cancer
46:  May cause heritable genetic damage
63:  Possible risk of harm to the unborn child
Safety Statements:
28:  After contact with skin, wash immediately with plenty of ... (to be specified by the manufacturer) 
36:  Wear suitable protective clothing 
37:  Wear suitable gloves
39:  Wear eye/face protection
45:  In case of accident or if you feel unwell, seek medical advice immediately (show label where possible)
63:  In case of accident by inhalation, remove casualty to fresh air and keep at rest
RIDADR: UN 2811 6.1/PG 1
WGK Germany: 3
RTECS: EK1750000
HazardClass: 6.1(b)
PackingGroup: III

Specification

  Busulfan , with CAS number of 55-98-1, can be called 1,4-Bis(methyl sulfonoxy)butane;busulphan ; 1,4-dimethanesulfonoxybutane ; 1,4-Butanediol dimethyl sulfonate; busulfex ; tetramethylene bis(methanesulfonate) . It is a white crystalline solid, Busulfan (CAS NO.55-98-1) can be used as alkylating agent with antileukemic activity. It can be used for antineoplastic.