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1,1-Cyclobutanedicarboxylic acid

HCID 2568
NotesReactions

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Basic informationNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
Substructure searchFind similar structures

Basic information

CAS
5445-51-2
Standard SMILES
O=C(O)C1(C(=O)O)CCC1
InChIKey
CCQPAEQGAVNNIA-UHFFFAOYSA-N
Molecular formula
C6H8O4
Average molar mass
144.12 g/mol
Monoisotopic mass
144.04225873

Names & identifiers

Preferred name
1,1-Cyclobutanedicarboxylic acid
IUPAC
cyclobutane-1,1-dicarboxylic acid
English name
1,1-Cyclobutanedicarboxylic acid
Molecular formula
C6H8O4
Molecular weight
144.13

Names & synonyms

1,1-Cyclobutanedicarboxylic acid5445-51-2Cyclobutane-1,1-dicarboxylic acidH2cbdca1,1-dicarboxycyclobutanePV866VZU2UEINECS 226-651-2NSC 22073NSC-22073DTXSID2063892CHEBI:356911-CARBOXYCYCLOBUTANECARBOXYLIC ACID
Show more names
1-Cyclobutanedicarboxylic acid226-651-21,1-CyclobutanedicarCarboplatin Impurity 1Carboplatin impurity Bobutane-1,1-dicarboxyL
RefChem:70999DTXCID5041724CCQPAEQGAVNNIA-UHFFFAOYSA-NInChI=1/C6H8O4/c7-4(8)6(5(9)10)2-1-3-6/h1-3H2,(H,7,8)(H,9,10Cyclobutanedicarboxylic acidMFCD00001325Carboplatin EP Impurity BCarboplatin Impurity 5

Database identifiers

CAS
5445-51-2
PubChem CID
2568
DTXSID
DTXSID2063892
ChEMBL
CHEMBL1162546
ChEBI
CHEBI:35691
UNII
PV866VZU2U
EC Number
226-651-2
Nikkaji
J208.210A

Properties

Computed structural propertiesFilling in

XLogP
0.4
Topological polar surface area
74.6 Ų
Hydrogen bond donors
2
Hydrogen bond acceptors
4
Rotatable bonds
2
Heavy atoms
10
Formal charge
0
Complexity
164

Physicochemical properties

Melting point
158 °C · 158 °C(lit.)
Boiling point
222.71 °C · 222.71°C (rough estimate)
Density
1.3217 · 1.3217 (rough estimate)
refractive index
1.58 · 1.5800 (estimate)
storage temp.
30 °C · Store below +30°C.
solubility
DMSO (Slightly), Methanol (Slightly)
pka
1 · pK1:3.13 ;pK2:5.88 (25°C)
form
Fine Crystalline Powder
color
White
BRN
2046031 · 2046031
InChI
InChI=1S/C6H8O4/c7-4(8)6(5(9)10)2-1-3-6/h1-3H2,(H,7,8)(H,9,10)
InChIKey
CCQPAEQGAVNNIA-UHFFFAOYSA-N
SMILES
C1(C(O)=O)(C(O)=O)CCC1
CAS DataBase Reference
5445 · 5445-51-2(CAS DataBase Reference)
FDA UNII
866 VZU2U · PV866VZU2U

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

GHS classification

GHS Classification · 6 items

This chemical does not meet GHS hazard criteria for 1.2% (1 of 83) of reports.

Danger

H314 (98.8%): Causes severe skin burns and eye damage [Danger Skin corrosion/irritation];H318 (27.7%): Causes serious eye damage [Danger Serious eye damage/eye irritation]

P260, P264, P264+P265, P280, P301+P330+P331, P302+P361+P354, P304+P340, P305+P354+P338, P316, P317, P321, P363, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 83 reports by companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.;Reported as not meeting GHS hazard criteria per 1 of 83 reports by companies.;There are 4 notifications provided by 82 of 83 reports by companies with hazard statement code(s).;Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website.

Hazard information

Regulatory Information · 2 items

Chemical: 1,1-Cyclobutanedicarboxylic acid

Status: Active Update: 15-05-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/25854

Hazard Classes and CategoriesSkin Corr. 1C (98.8%);Eye Dam. 1 (27.7%)

Toxicology

Effects During Pregnancy and Lactation · 1 item

◉ Summary of Use during Lactation;After carboplatin administration to nursing mothers, excretion of platinum into milk occurs. The exact forms and toxicities of platinum excreted into breastmilk are not known. The nursing infant would receive platinum compounds orally rather than intravenously and oral absorption of platinum compounds by infants is not known. Platinum in milk may increase with repeated courses of chemotherapy. Most sources consider that mothers receiving antineoplastic therapy should not breastfeed, especially with alkylating agents such as cisplatin. It is probably not safe to breastfeed during carboplatin therapy, and breastfeeding should be discontinued. Resuming breastfeeding 3 weeks after the last dose of cisplatin has been done safely in one case.;Chemotherapy may adversely affect the normal microbiome and chemical makeup of breastmilk. Women who receive chemotherapy during pregnancy are more likely to have difficulty nursing their infant.;◉ Effects in Breastfed Infants;Relevant published information was not found as of the revision date.;◉ Effects on Lactation and Breastmilk;A telephone follow-up study was conducted on 74 women who received cancer chemotherapy at one center during the second or third trimester of pregnancy to determine if they were successful at breastfeeding postpartum. Only 34% of the women were able to exclusively breastfeed their infants, and 66% of the women reported experiencing breastfeeding difficulties. This was in comparison to a 91% breastfeeding success rate in 22 other mothers diagnosed during pregnancy, but not treated with chemotherapy. Other statistically significant correlations included: 1. mothers with breastfeeding difficulties had an average of 5.5 cycles of chemotherapy compared with 3.8 cycles among mothers who had no difficulties; and 2. mothers with breastfeeding difficulties received their first cycle of chemotherapy on average 3.4 weeks earlier in pregnancy. Of the 3 women who received a regimen containing the similar drug, cisplatin, 1 had breastfeeding difficulties.

Chemistry & industry

Uses & manufacturing

General Manufacturing Information1,1-Cyclobutanedicarboxylic acid: ACTIVE
Applications · 2 items

Uses1,1-Cyclobutanedicarboxylic Acid(5445-51-2) is used in the design, studies and structural model of antitumor dicycloplatin a clinical cancer drug. Hydrolysis mechanism of second-generation anticancer drug carboplatin.

UsesCyclobutane-1,1-dicarboxylic acid can be used as: A reactant to synthesize lithium coordination polymer by treating with lithium carbonate. A ligand to prepare various lanthanide metal-organic frameworks (LnMOFs) via a solvothermal method. Eu+3 based MOF is applicable as a selective chemical sensor for detecting CH3OH due to its high luminescence quantum yield.It can also be used as a starting material in the synthesis of carboplatin (cis-diammine(1,1-cyclobutanedicarboxyl-ate)platinum(II)).

Upstream & downstream products

Upstream raw materials

Sodium ethoxideSodium MethoxideDiethyl azodicarboxylateBromine1-Bromo-3-chloropropane

Downstream products

ZENIPLATINCyclobutanecarboxylic acidCarboplatinENLOPLATINDiethyl 1,1-cyclobutanedicarboxylate

Related reactions

8 records
New reaction record
HRID 445459 reaction equation
HRID 445459As reactantuspto-grants-2013_07
HRID 455813 reaction equation
HRID 455813As reactantuspto-grants-2013_07
HRID 562981 reaction equation
HRID 562981As reactantuspto-grants-2011_11
HRID 705618 reaction equation
HRID 705618As reactantuspto-grants-2015_11
HRID 1145661 reaction equation
HRID 1145661As reactantTraining data from https://doi.org/10.1039/C8SC04228D (7/10)
HRID 1245561 reaction equation
HRID 1245561As reactantuspto-grants-2006_10
HRID 1924141 reaction equation
HRID 1924141As reactantuspto-grants-2012_05
HRID 2106108 reaction equation
HRID 2106108As reactantuspto-grants-2009_08

Compound notes

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On this pageBasic informationNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
NIST Chemistry Reference
1 · 1,1-Cyclobutanedicarboxylic acid(5445-51-2)
EPA Substance Registry System
1 · 1,1-Cyclobutanedicarboxylic acid (5445-51-2)
UNSPSC Code
12352106 · 12352106
NACRES
22 · NA.22
Symbol(GHS)
5 · GHS05
Signal word
Danger
Hazard statements
314 · H314
Precautionary statements
260 · P260-P280-P303+P361+P353-P304+P340+P310-P305+P351+P338-P363
PPE
3 · Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges
Hazard Codes
C
Risk Statements
34 · 34
Safety Statements
26 · 26-36/37/39-45-28A
RIDADR
3261 · UN 3261 8/PG 2
WGK Germany
3 · 3
RTECS
1335000 · GU1335000
Hazard Note
Corrosive
TSCA
TSCA listed
HazardClass
8 · 8
PackingGroup
III
HS Code
29172000 · 29172000
Storage Class
8 A · 8A - Combustible corrosive hazardous materials
Hazard Classifications
1 B · Skin Corr. 1B
REACH Registrations
Active
Limited Quantities
1 Kg · 1 Kg (2.2 lbs) (solid)
Excepted Quantities
Max Inner Pack (30g or 30ml) and Max Outer Pack (500g or 500ml)

Regulatory information

Regulatory Information · 2 items

Chemical: 1,1-Cyclobutanedicarboxylic acid

Status: Active Update: 15-05-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/25854

Safety data

PPE
Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges
wgk
3
tsca
TSCA listed
rtecs
GU1335000
ridadr
UN 3261 8/PG 2
hs_code
29172000
risk_code
34
Signal word
Danger
Symbol(GHS)
GHS05
hazard_code
C
hazard_note
Corrosive
safety_code
26-36/37/39-45-28A
hazard_class
8
Storage Class
8A - Combustible corrosive hazardous materials
packing_group
III
Hazard statements
H314
Limited Quantities
1 Kg (2.2 lbs) (solid)
Excepted Quantities
Max Inner Pack (30g or 30ml) and Max Outer Pack (500g or 500ml)
REACH Registrations
Active
Hazard Classifications
Skin Corr. 1B
Precautionary statements
P260-P280-P303+P361+P353-P304+P340+P310-P305+P351+P338-P363
2-azaspiro[3.3]heptane
Cyclobutanecarbonitrile
Cyclobutanecarbonyl chloride
Cyclobutanemethanol

Suppliers100 total

国药集团化学试剂有限公司86-21-63210123 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
INTATRADE GmbH+49 3493/605464 · [email protected]
中节能万润股份有限公司0535-6101880 · [email protected]
T&W GROUP021-61551611 13296011611 · [email protected]
山东前元高分子材料有限公司18678041314 18765609661 · [email protected]
韶远科技(上海)有限公司4000665055 · [email protected]
科瑞迪化学400-821-5857 021-64326257 · [email protected]
上海将来实业股份有限公司400-0066400 13621662912 · [email protected]
Syntechem Co.,Ltd[email protected]
上海迈瑞尔生化科技有限公司4006356688 18621169109 · [email protected]
宁波亿诺化学品有限公司86-574-27787657 · [email protected]
阿法埃莎(中国)化学有限公司400-6106006 · [email protected]
太原市瑞和丰科贸有限公司+86 351 7031519 · [email protected]
安耐吉化学&3A(安徽泽升科技股份有限公司)400-0056266 · [email protected]
常州安轩化工有限公司13912302692 · [email protected]
上海瀚鸿科技股份有限公司021-54306202 13764082696 · [email protected]
上海柯维化学技术有限公司021-64609169 18901607656 · [email protected]
上海相辉医药科技有限公司13761987713 · [email protected]
山东丰金制药有限公司15898960031 15898960031 · [email protected]
常州环灵化工有限公司89803005 18206112582 · [email protected]
嘉兴市艾森化工有限公司0573-85285100 18627885956 · [email protected]
Pure Chemistry Scientific Inc.001-857-928-2050 or 1-888-588-9418 · [email protected]
上海隆盛化工有限公司58099637 13585536065 · [email protected]
武汉丰泰威远科技有限公司027-87465837 19945049750 · [email protected]
孝感深远化工有限公司15527621225; 15527621225 · [email protected]
济南精合医药科技有限公司0531-88811783 · [email protected]
唐山默内德贸易有限公司0315-8309571 15633399667 · [email protected]
成都格蓝洋生物医药科技有限公司86+28-85337952 18081025021 · [email protected]
天津希恩思生化科技有限公司400 638 7771 · [email protected]
同创医药(苏州)有限公司0512-63263366 18912765016 · [email protected]
上海乔木化学科技有限公司021-60451683 15021268886 · [email protected]
艾科试剂4008-755-333 18080918076 · [email protected]
上海思域化工科技有限公司86-21-34053660 · [email protected]
赛默飞世尔科技(中国)有限公司800-810-5118 · [email protected]
北京伊诺凯科技有限公司400-810-7969 010-59572699 · [email protected]
江苏艾康生物医药研发有限公司025-66113011 13913916777 · [email protected]
TCI AMERICA800-4238616 · [email protected]
TOKYO CHEMICAL INDUSTRY CO., LTD.03-36680489 · [email protected]
TCI Europe320-37350700 · [email protected]
上海贤鼎生物科技有限公司4009209199 · [email protected]
深圳振强药物研发有限公司0755-66853366 13670046396 · [email protected]
深圳康特腾科技有限公司86-0755-86635001 · [email protected]
上海睿升化工科技有限公司+86-021-50935922
Clearsynth Labs Limited+91-22-26355700 · [email protected]
广州爱纯医药科技有限公司020-39119399 18927568969 · [email protected]
苏州爱玛特生物科技有限公司0512-56316828 4008675858 · [email protected]
上海湄水化工科技有限公司021-60549325 18616193163
上海将来实业股份有限公司400-0066400 13621662912 · [email protected]

Additional notes

DefinitionChEBI: Cyclobutane-1,1-dicarboxylic acid is a cyclobutanedicarboxylic acid. It is a conjugate acid of a cyclobutane-1,1-dicarboxylate(1-).